Propionic Acid → HCID 12741429, compound

Participants

Reaction Steps

Sodium borohydride (26.85 g, 0.71 mol) was added in small portions to propionic acid (172.2 mL, 2.3 moles) in dry benzene (650 mL), maintaining the temperature below 20° C. When hydrogen evolution ceased, a solution of N-propyl-6-methoxy-1,2,3,5-tetrahydro-2-naphthylamine (30.93 g, 0.141 mol) in benzene (150 mL) was added and the resulting mixture was refluxed for 3 hr. The cooled mixture was shaken with excess 10% (w/v) sodium hydroxide solution. The organic layer was separated, dried over MgSO4 and evaporated to give a brown oil of N,N-dipropyl-6-methoxy-1,2,3,4-tetrahydro-2-naphthylamine, NMR (CDCl3) δ 0.85 (t, 6H), 1.45 (m, 6H), 2.45 (t, 4H), 2.7 (m, 5H), 3.70 (s, 3H) and 6.7 (m, 3H).

Provenance & Evidence